


Sugar Baby

by Everyday_Im_Preaching



Category: Xiaolin Showdown (Cartoon)
Genre: Alternate Universe, Kissing, M/M, Masturbation, Misunderstandings, Sugar Baby! Jack, Sugar Daddy! Chase, Voyeurism, consensual voyeurism, modern!AU, poor!Jack, sugar baby!au
Language: English
Status: Completed
Published: 2017-11-17
Updated: 2017-11-17
Packaged: 2019-02-03 17:04:31
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,451
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12752523
Author URL: https://archiveofourown.org/users/Everyday_Im_Preaching/pseuds/Everyday_Im_Preaching
Summary: It had started with a fair amount of innocence attached to it—in a desperate, final attempt to pay for his next semester, Jack had signed up for a sugar baby site.In the end, Jack can't decide if it's the best decision he's made, or the worst.





	Sugar Baby

**Author's Note:**

> Hi guys! Look what I have for you!  
> A fic that I wanted to write 20+ chapters for but settled on writing a single chapter for ;u; if you want to see more of/learn more of this AU, please let me know in the comments below! Or, hey, if you just like it and want to leave a comment, that's okay too!
> 
> Edit: Jack is twenty-two and Chase is thirty-six. Just for clarification.

 

 

It had started with a fair amount of innocence attached to it—in a desperate, final attempt to pay for his next semester, Jack had signed up for a sugar baby site. It wasn’t his first option, naturally, but a part-time job wouldn’t cover his tuition. Jack had exhausted scholarships, and his grandma had about as much money as he did—he couldn’t ask her for any more than she already attempted to give.

The first man to contact Jack was, luckily, the last one. He’d introduced himself as Chase Young in a cordial, polite message, inquiring about Jack’s school and the money needed to cover the cost to earn his degree. Jack had replied readily—it wasn’t like he was hiding the reason he was there, after all.

Site correspondence with Chase had turned into texts, and texts turned into phone calls. And then phone calls turned into requests to meet, and meeting had turned into— _ this.  _ Jack’s job.

Jack’s job was simple. For three hours a day, three days a week, Jack would sit in complete silence in the corner of Chase’s office. Usually it was in the evening, and over the weekend, whilst the business mogul worked. Jack was required to dress in traditional Chinese dress (that Chase had purchased), as well as a full face of makeup.

The requests were odd, at first, since Chase rarely looked at Jack while he was there. It made him feel more like a trophy than a companion, but the job paid a thousand a night for what seemed like  _ minimal  _ effort. There was a decorative, comfy chaise that Jack was to sit on for the encounter—as long as he was quiet, he was allowed to nap, eat from a nearby platter of finger sandwiches and fruit, or fidget with his phone. Not to mention the credit card that Chase had handed him on their third meeting, telling him to purchase whatever he needed with it, clothes included.

And in the end, Jack was mentally kicking himself for thinking that that’s all that Chase wanted.

Halfway through one of their Saturday evenings together, Chase had risen from his chair and prowled over to Jack, looking far too predatory for the young man’s comfort. He’d stopped a good five feet from Jack, looking him over with hungry eyes.

“Masturbate for me.” The words were smooth and rumbled forward from somewhere deep in Chase’s throat. Jack let out a choked, strangled noise at the request. Jack opened his mouth to reply, but Chase rose a hand to stop him. “If you pleasure yourself in front of me, I will pay you the rest of the money that you require to pay for not only this semester's tuition, but for your books as well.” 

Jack looked at the man in front of him, mildly put off by the statement—but also  _ very  _ intrigued. That was a lot of money—and Jack knew that Chase was good for it. Jack went to fiddle with his fingers, drawing his bottom lip into his mouth as he thought. 

“You… you’re going to pay for my school, just to watch me masturbate.” It was a statement, not a question. Jack didn’t think he could have made it sound like a question, no matter how hard he tried.

Chase nodded at him, folding his arms behind his back. “I know you wish to ask why. It is simple—I want to see your face when you reach climax.” He tilted his head to the side. “In fact, if you agree, I will send half of the required amount to you this very instant.”

A low hum left Jack; he was genuinely considering the offer. Again, it was a lot of money, and he was  _ very  _ broke. He took a deep breath and swung his legs over the side of the couch, looking at his feet.

“There is no shame in it,” Chase told him gently. “And I will not touch you. I simply desire to watch.”

After another moment or two, Jack found himself nodding. “Yeah,” he replied, letting his eyes flicker up to meet Chase’s. “I’ll… I’ll do it.” 

Jack expected some sort of outward response from Chase, but the older man simply walked over to his desk and picked up his cellphone. He fiddled with it for a moment, and then placed it face down on his desk once more. Seconds later, Jack’s phone vibrated beneath him; slipping it out from under his leg, he opened it with shaking fingers.

His heart  _ dropped,  _ and his mouth went dry when he saw the amount that had been deposited into his account. Jack slowly let his eyes wander over to Chase, who was looking at him expectantly. The college student swallowed, then placed his phone on the snack table. 

“Can you lock the door?” Jack asked quietly, rubbing at his shoulder.  _ Gods,  _ he was nervous. He’d never thought that he’d masturbate in front of  _ anyone.  _ And especially not for money.

“Of course,” Chase agreed seamlessly, crossing the room with a purposeful stride. The lock clicked into place, and Chase pressed a finger against the speaker next to the door. “Sharlene, would you cancel my appointments for the evening?” A tinny, female voice responded affirmatively. 

“Oh, shit, I’m sorry. I didn’t mean you had to cancel your appointments,” Jack told Chase when the older man had dropped his hand away from the button.

“You are my new appointment,” Chase replied, eye only twitching slightly at Jack’s swear.

Jack swallowed again, and then ran his hands down his chest, shuddering when his palms brushed his nipples through the thick fabric of his  _ hanfu.  _ “Do you… do you want to pull up a chair or something?” He asked, letting his hands skate over his belly. 

“Would you be comfortable with such a thing?” Chase asked, voice quiet. Jack’s breath hitched as his palm skated the area above his crotch. Everything seemed sensitive, with a stranger’s eyes on him—and Chase  _ was  _ a stranger. Yes, the man paid him, but it wasn’t like the two had ever conversed or gotten to know each other. 

The realisation was yet another stone sinking into his belly of uncertainties. But he’d already agreed, and Chase had sent him so much money already. “Yeah, I think it’d be easier on your feet. I have to kind of… work myself up to it.” 

Chase didn't respond to this, face remaining neutral as he went and retrieved a wooden chair from the other side of the room. He took a moment to arrange it, making sure the angle was correct before settling down into it.

“Go ahead and lay back, if it makes you comfortable. And please.” Chase leaned forward, steepling his fingers. “Don’t muffle yourself. I want to hear you.”

“Will Sharlene hear us?” Jack asked as he swung his legs up and stretched out on the chaise. Once again, he ran his hands down his body, light and gentle as they skated over his chest. Jack pinched at his nipples, rolling them as best he could on the outside of his clothes. His heart was racing, reminding him of  _ what  _ exactly he was doing with every heavy thud against his ribcage.

“She shouldn’t,” Chase replied, words barely above a whisper. Jack gathered enough energy to look at the business man. He was dressed in a fine, black suit, and had his hair gathered in a ponytail behind his head. Near-yellow eyes were undressing Jack with every flick, starving to catch a glimpse of actual  _ skin  _ beneath the robes that Jack wore.

Jack almost groaned and let his eyes drift close. Chase was  _ hot.  _ Chase was a handsome, middle aged man that was going to pay him over twenty thousand dollars to  _ jerk off  _ in his office. On his couch.  _ In clothing that Jack would never have been able to pay for.  _ This had to be some sort of fucked up fever dream.

Letting one of his hands wander down, taking in a shaky breath as he palmed himself. It wouldn’t be that hard to get an erection—in fact, the entire situation was making him far more sensitive than normal. The drag of cloth against his cock was enticing, sending small jolts of pleasure up through his body to jerk at his shoulders. 

“Fuck,” Jack breathed, licking at dry lips. He let the hand on his crotch rub against the inside of his thigh, bunching up the fabric. Working the heavier layers off his torso, he let them fall onto the chaise behind him—Chase was paying him, so he should put on a show, right? A little bit? That was reasonable.

Jack slid a hand into the layer of cloth that remained, gently pinching one of his nipples between his fingers and tugging on it. Chase grunted in response, and Jack could hear him shift in the chair. 

“Take all the time you need,” Chase murmured. “Don’t rush yourself for me.”

The younger man swallowed hard and nodded, letting out a soft whimper when one of his nails scraped a nipple. He bit at his bottom lip, beginning to undo the tie there. It would have been easier with jeans, but pants were pants, and the eventually had to come off if this was going to work. 

Jack let out a low groan, but not because he had touched himself. No, he groaned because of the choked noise that left Chase’s throat as Jack tugged his cock free from his  _ hakama _ . Again, the chair shifted, and Jack felt an odd sort of pride swelling in his chest—it was quickly drowned out by embarrassment as he realised that Chase was staring at him.

_ It’s kind of arousing,  _ Jack thought to himself, cracking an eye open. 

Chase had one hand loosely gripping the front of his trousers, eagerly leaning forward in his chair as Jack slowly pumped himself. Chase’s eyes were dancing between Jack’s cock and his face, unsure of which one he wanted to look at more. Jack, feeling brave, caught the businessman’s eye and groaned, partially arching up off the couch as he slid his thumb across the slit at the top of his cock.

The shudder that went through Chase was  _ beautiful,  _ vibrating through his body with a half-assed attempt at hiding a groan. Jack felt  _ powerful,  _ digging his heel into the soft cushioning beneath him and arching his hips slightly upward. The sound of Chase’s chair screeching backward had Jack’s eyes popping open and widening. His hand flew away from his cock, and he kicked up on the chaise, away from the older man.

“C… Continue,” Chase rumbled out, though his chest was heaving and Jack could see the outline of his dick pressing against the front of his pants. “Sorry if I frightened you. I did not intend too.”

Jack waited until Chase took to his seat once more. He shyly cupped himself once again, biting at his lips as a whimper left him. He didn’t shy away from Chase’s gaze this time, hard and eager enough to smear his own pre-cum down his cock in languid strokes.

He thought that he’d need to immerse himself in fantasy—but it was enough to have Chase’s eyes on him. It was enough to know that a man he barely knew was  _ getting off  _ on him, well, getting off. It made him twist his hips a little bit harder up into his hand. It made him pinch and tug at his nipples more than normal, until they were sore and sensitive under his fingers.

Before Jack knew it, one of his hands was gripping tightly at the back of the couch whilst his other was covered in sticky, rapidly cooling cum. The sound of Chase growling out something or another vaguely rang in his ears, and Jack smiled, partially dazed from his own orgasm. 

It seemed like mere minutes later, but Jack knew it had been longer.

“Jack.” Chase said his name like a prayer, now standing at Jack’s feet. He looked up at Chase, who was holding a damp towel and a cup of water. “I’ve sent the rest of the money to your account. You did well.” Jack, slightly jelly-limbed and unsure, threw his legs over the side of the couch and took both of the items. 

“Ah, uh, thank you?” Jack muttered out, setting the cup aside so he could begin cleaning himself. Chase nodded, keeping his eyes on Jack’s face. “So, um.”

Chase cut him off, before he could ask anything. “I hope that you will grace me with your presence tomorrow evening. I would hate for this to ruin our arrangement—you may use my personal bathroom to change into your normal clothing, if you wish. I don’t imagine that you want to leave in anything stained.”

“Yeah, that’d… that’d be nice,” Jack squeaked out, tucking his dick back into his underwear. “Will I…?”

The businessman shook his head. “No. And never against your will. If I require such a thing again, be assured that you will be paid handsomely.” Chase reached a hand out, hand twitching before pulling it back to himself. There was a question on the tip of Chase’s tongue—Jack had an inkling of what it was. In fact, he was sure he knew.

“You can,” Jack suddenly said. “If you want to.” 

Chase’s hand came to gently rest on Jack’s face, sliding up to wind in the bright red locks of Jack’s hair. Jack’s head was tilted backward, and cold lips pressed against his in a semi-chaste kiss. Jack let out an uncertain noise into Chase’s mouth; however, when a blunt tongue pressed against his mouth, he let it in without question.

Maybe Jack  _ didn’t  _ know what Chase was thinking.

“Thank you,” Chase breathed against Jack’s lips. His body was pressing between Jack’s legs, and his mouth was kissing at Jack’s cheeks and nose. Jack gasped as he felt a still-hard cock press against his thigh as he was pressed down against the couch.

_ Oh, fuck. Wrong idea, wrong idea.  _ Jack internally panicked, even as a hot mouth travelled down the side of his neck.  _ Oh, but such a  _ good  _ idea.  _ He mentally whined as Chase’s hips ground against his. Even as oversensitive as he was, the pressure was welcome. 

“I’ll pay extra for this service, if you intend to provide it on a regular basis,” Chase huffed into his ear, rutting enthusiastically against Jack. Jack whimpered in Chase’s ear, hooking an arm around Chase’s neck. “Unless you’d like to stop, we can work out the details later.”

“Later,” Jack agreed with a gasp, feeling wandering fingers grab at his ass. “ _ Definitely  _ later.”

**Author's Note:**

> Well hello again!  
> Special thanks to ivory-imperium for giving me the idea for this!
> 
> Want to stay updated? Click [here](http://everyday-im-preaching.tumblr.com/) to stay in the know!


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